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  • 1.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Larsson, Rikard
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Introducing Dynamic Combinatorial Chemistry: Probing the Substrate Selectivity of Acetylcholinesterase2010Inngår i: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, nr 11, s. 1248-1251Artikkel i tidsskrift (Fagfellevurdert)
  • 2.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Larsson, Rikard
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dynamic combinatorial resolution2009Inngår i: Dynamic Combinatorial Chemistry: In Drug Discovery, Bioorganic Chemistry, and Materials Science / [ed] Miller, B., John Wiley & Sons, 2009, s. 169-200Kapittel i bok, del av antologi (Fagfellevurdert)
  • 3.
    Angelin, Marcus
    et al.
    KTH, Skolan för industriell teknik och management (ITM).
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE).
    Fischer, Andreas C.
    KTH, Skolan för kemivetenskap (CHE).
    Ramstrom, Olof
    KTH, Skolan för kemivetenskap (CHE).
    ORGN 103-Tandem driven dynamic libraries: Amplification through internal selection pressure2007Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 234Artikkel i tidsskrift (Annet vitenskapelig)
  • 4.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Crystallization Driven Asymmetric Synthesis of Pyridine β-Nitroalcoholsvia Discovery-Oriented Self-Resolution of a Dynamic System2010Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 33, s. 6315-6318Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The study of dynamic nitroaldol systems aided the discovery of a diastereoselective crystallization process through amplification of 2-nitro-1-(pyridine-4-yl)propan-1-ol. The phenomenon was further developed into an effective procedure for asymmetic synthesis of pyridine-nitroalcohols and several substrates were screened to this end. These results demonstrate how work with larger dynamic systems facilitates and increases the likelihood of serendipitous discoveries.

  • 5.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Tandem driven dynamic combinatorial resolution via Henry–iminolactone rearrangement2008Inngår i: ChemComm, ISSN 1359-7345, s. 768-770Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An unexplored type of tandem reaction is used to kinetically resolve a dynamic combinatorial library resulting in quantitative amplification of an interesting 3-substituted isoindolinone.

  • 6.
    Caraballo, Remi
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Rahm, Martin
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Brinck, Tore
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Phosphine-catalyzed disulfide metathesis2008Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, nr 48, s. 6603-6605Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The reaction between disulfides and phosphines generates a reversible disulfide metathesis process.

  • 7.
    Larsson, Rikard
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Angelin, Marcus
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    ORGN 231-Dynamic catalytic screening of hydrolase substrates from adaptive combinatorial thiolester libraries2006Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 232Artikkel i tidsskrift (Annet vitenskapelig)
  • 8.
    Larsson, Rikard
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Angelin, Marcus
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dynamic Combinatorial Resolution2007Inngår i: Materials, Membranes and Processes / [ed] G. Nechifor and M.Barboiu, Bucharest: Printech , 2007, s. 30-65Kapittel i bok, del av antologi (Annet vitenskapelig)
  • 9.
    Sakulsombat, Morakot
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in alpha-Aminonitrile Resolution2014Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, nr 36, s. 11322-11325Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic alpha-aminonitrile compounds are described. alpha-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates.

  • 10.
    Sakulsombat, Morakot
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    In Situ Evaluation of Lipase Performances Through Dynamic Asymmetric Cyanohydrin Resolution2011Inngår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 9, nr 4, s. 1112-1117Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A dynamic resolution process based on multiple reversible cyanohydrin formation coupled to lipase-mediated transesterification is demonstrated. The resulting process resulted in the efficient evaluation of complex lipase performances in asymmetric cyanohydrin acylate synthesis. Dynamic systems were generated and resolved in situ, and the effects of the reaction conditions could be directly monitored for the overall system. By this concept, the enzyme activity, chemo- and stereoselectivity for all involved substrates could be simultaneously evaluated.

  • 11.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Dynamic Covalent Resolution: Applications in System Screening and Asymmetric Synthesis2009Doktoravhandling, med artikler (Annet vitenskapelig)
    Abstract [en]

    Combined thermodynamic/kinetic events amount to a kinetically controlled Dynamic Combinatorial Resolution (DCR) process, where the lability of themolecules/aggregates are used to generate dynamics, and the species experiencing the lowest activation energy is selected via kinetic process. Bothinter- and intramolecular processes can be performed using this concept,resulting in complete resolution and associated amplification of the selected species. When intermolecular processes are resolved using this method, an additional advantage is that only a catalytic amount of selector is required tocontrol the system.In this thesis, the Henry and Strecker reactions were developed as efficient C–C bond-forming routes to single and multi-level dynamic covalent systems.These methods efficiently provided a vast variety of substrates from smallnumbers of starting compounds. These dynamic systems, generated underthermodynamic control at mild conditions, were coupled in one-pot processes with kinetically controlled lipase-mediated transacylation. The enzym emediated resolution of the dynamic nitroaldol system led to enantiomericallypure β-nitroacetates in high yield. Furthermore, combination of multi-leveldynamic Strecker systems and lipase-mediated acylation resulted in theresolution of specific α-aminonitriles from the pool.In addition, the asymmetric synthesis of discrete β-nitroalkanol derivatives wassimply achieved, resulting in high yields and high enantiomeric purities through the direct one-pot procedure. Moreover, racemase type activity oflipase enzyme through N-substituted α-aminonitrile structure has been discovered. By use of control experiments together with molecular modeling,the mechanism of the racemization process has been established. Asymmetric synthesis of N-methyl α-aminonitriles was also performed through the dualfunction of lipase, resulting in high yield and good enantio selectivity.

  • 12.
    Vongvilai, Pornrapee
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Angelin, Marcus
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Larsson, Rikard
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dynamic Combinatorial Resolution: Direct Asymmetric Lipase-Mediated Screening of a Dynamic Nitroaldol Library2007Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, nr 6, s. 948-950Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    (Chemical Equation Presented) A disturbance in the library: The nitroaldol (Henry) reaction was developed as an efficient C-C bond-forming route to dynamic combinatorial libraries (DCLs). These DCLs generated under thermodynamic control were coupled in a one-pot process with kinetically controlled lipase-mediated transesterification (see scheme). The asymmetric resolution of the DCLs by the enzyme led to enantiomerically pure β-nitroacetates in high yield.

  • 13.
    Vongvilai, Pornrapee
    et al.
    KTH, Skolan för kemivetenskap (CHE).
    Angelin, Marcus
    KTH, Skolan för kemivetenskap (CHE).
    Larsson, Rikard
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Kemi, Organisk kemi.
    Dynamic combinatorial resolution: Direct substrate identification in asymmetric lipase-mediated transacylations.2009Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 238Artikkel i tidsskrift (Annet vitenskapelig)
  • 14.
    Vongvilai, Pornrapee
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Larsson, Rikard
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Direct Asymmetric Dynamic Kinetic Resolution by Combined Lipase Catalysis and Nitroaldol (Henry) Reaction2008Inngår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 350, nr 3, s. 448-452Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The asymmetric synthesis of β-nitroalkanol derivatives was simply achieved by a combined nitroaldol (Henry) reaction with lipase-catalyzed transesterification in high yield and enantiomeric purity (up to 92% and 99% ee) through a direct one-pot procedure.

  • 15.
    Vongvilai, Pornrapee
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Linder, Mats
    KTH, Skolan för kemivetenskap (CHE), Kemi, Fysikalisk kemi (stängd 20110630).
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Humble, Maria Svedendahl
    KTH, Skolan för bioteknologi (BIO), Biokemi.
    Berglund, Per
    KTH, Skolan för bioteknologi (BIO), Biokemi.
    Brinck, Tore
    KTH, Skolan för kemivetenskap (CHE), Kemi, Fysikalisk kemi (stängd 20110630).
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Racemase Activity of B. cepacia Lipase Leads to Dual-Function Asymmetric Dynamic Kinetic Resolution of alpha-Aminonitriles2011Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, nr 29, s. 6592-6595Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Applaudable promiscuity: Racemase-type activity discovered for B. cepacia lipase with N-substituted α-aminonitriles is proposed to involve a C-C bond-breaking/forming mechanism in the hydrolase site of the enzyme, as supported by experimental data and calculations. This promiscuous activity in combination with the transacylation activity of the enzyme enabled the asymmetric synthesis of N-methyl α-aminonitrile amides in high yield (see scheme).

  • 16.
    Vongvilai, Pornrapee
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Dynamic Asymmetric Multicomponent Resolution: Lipase-Mediated Amidation of a Double Dynamic Covalent System2009Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 131, nr 40, s. 14419-14425Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The Strecker reaction is one of the most important multicomponent reactions developed, leading to alpha-aminonitriles that are versatile substrates for many synthetic applications. In the present study, this reaction type has been applied to a double dynamic covalent resolution protocol, leading to efficient C-C- and C-N-bond generation as well as chiral discrimination. The combination of transimination with iminecyanation enabled the dynamic exchange in more,than one direction around a single stereogenic center of restricted structure. This multiple exchange process could generate a vast range of compounds from a low number of starting materials in very short time. The resulting double dynamic covalent systems, created under thermodynamic control, were subsequently coupled in a one-pot process with kinetically controlled lipase-mediated transacylation. This resulted in complete resolution of the dynamic systems, yielding the optimal N-acyl-alpha-aminonitriles for the enzyme, where the individual chemoenzymatic reactions could produce enantiomerically pure acylated N-substituted alpha-aminonitriles in good yields.

  • 17.
    Vongvilai, Pornrapee
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    In Situ Evaluation of Lipase Performances Through Dynamic Asymmetric Cyanohydrin ResolutionManuskript (preprint) (Annet vitenskapelig)
  • 18. Zhang, Yan
    et al.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Hu, Lei
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Lipase-mediated dynamic systemic resolution based on single or double reversible reactions2012Inngår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 244Artikkel i tidsskrift (Annet vitenskapelig)
  • 19.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi, Tillämpad fysikalisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael-Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis2014Inngår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, nr 5, s. 987-992Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

  • 20.
    Zhang, Yan
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sakulsombat, Morakot
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Biocatalyzed Dynamic Systemic Domino Thia-Michael--Henry Resolution to Substituted Asymmetric ThiolanesArtikkel i tidsskrift (Annet vitenskapelig)
    Abstract [en]

    Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

1 - 20 of 20
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  • en-GB
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  • fi-FI
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